Triethylamine → HCID 18545197, compound

HRID 1266998Notes

Reaction equation

HRID 1266998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:23][C:24]([F:37])([F:36])[C:25]([NH:27][CH2:28][CH2:29][CH2:30]OS(C)(=O)=O)=[O:26]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH:10]3[N:15]([CH2:30][CH2:29][CH2:28][NH:27][C:25](=[O:26])[C:24]([F:37])([F:36])[F:23])[CH:13]([CH2:12][CH2:11]3)[CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98592793-(4-chlorophenyl)-8-azabicyclo[3.2.1]oct-2-eneHCID 86585100HCID 86585100, compound

Product 1

HCID 18545197HCID 18545197, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Racemic 3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-ene (1.0 g, 4.55 mmol), triethylamine (0.70 mL, 5.01 mmol), and methanesulfonic acid 3-(2,2,2-trifluoro-acetylamino)-propyl ester (1.13 g, 4.55 mmol) in ethanol (20 mL) were refluxed for 15 hours. The mix was concentrated, diluted with saturated sodium bicarbonate (200 mL) and extracted with ethyl acetate (3×150 mL). Combined organic layers were washed with brine (200 mL), dried with magnesium sulfate and concentrated to a light brown oil. Silica gel flash chromatography using 5% methanol/chloroform as the eluent yielded racemic N-{3-[3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-en-8-yl]-propyl}-2,2,2-trifluoro-acetamide (0.79 g, 46.5%) as a light brown oil which had the following properties: 1H NMR CDCl3 δ: 10.00 (brd s, 1H), 7.27 (s, 4H), 6.23 (d, J=5.4 Hz, 1H), 3.69-3.43 (m, 4H), 2.82-2.71 (m, 3H), 2.19-1.88 (m, 4H), 1.77-1.57 (m, 3H). IR (CHCl3): 3157, 2949, 2880, 1714, 1544, 1494, 1466, 1446, 1403, 1377, 1346, 1315, 1245, 1162, 1094, 1012, 973, 937, 817, (cm−1). Analysis calculated for C18H20ClF3N2O.3/4 H2O: C, 55.96; H, 5.61; N, 7.25; Found: C, 55.80; H, 5.09; N, 7.33.

Workup

  1. concentrationThe mix was concentrated
  2. additiondiluted with saturated sodium bicarbonate (200 mL)
  3. extractionextracted with ethyl acetate (3×150 mL)
  4. washCombined organic layers were washed with brine (200 mL)
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated to a light brown oil

Sources & evidence

ORD record
ord-635dac2ddeee4f18a6c59600f2daa68a
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

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